One‐pot sequential regioselective intramolecular synthesis of furo[3,2‐c]chromen and imidazo[1,2‐a]pyridine via catalyst‐free and basic conditions

We developed a sequential intramolecular ring‐closure‐opening‐closure pathway using a catalyst‐free and organo‐base catalyzed system for the synthesis of fused regioselective tricyclic furo[3,2‐c]chromen and bicyclic imidazo[1,2‐a]pyridine via a one‐pot three‐component reaction. The protocol involve...

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Bibliographic Details
Published in:Journal of heterocyclic chemistry 2023-12, Vol.60 (12), p.2053-2062
Main Authors: Yadav, Maruti B., Yeon, Tae Jeong
Format: Article
Language:English
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Summary:We developed a sequential intramolecular ring‐closure‐opening‐closure pathway using a catalyst‐free and organo‐base catalyzed system for the synthesis of fused regioselective tricyclic furo[3,2‐c]chromen and bicyclic imidazo[1,2‐a]pyridine via a one‐pot three‐component reaction. The protocol involved a Knoevenagel and Michael adduct via intramolecular cyclization with 4‐hydroxycoumarin, aromatic glyoxal, and 2‐aminopyridine under heating and ambient conditions with very good yields. The merits of this methodology were studied, and new practical ways were developed to access furo[3,2‐c]chromen and imidazo[1,2‐a]pyridine moieties. Regioselective Intramolecular Synthesis of Furo[3,2‐c]chromen and Imidazo[1,2‐a]pyridine derivatives.
ISSN:0022-152X
1943-5193
DOI:10.1002/jhet.4735